Methyl iodide → 2-Fluoro-6-nitroanisole

Participants

Reaction Steps

A solution of 2-fluoro-6-nitrophenol (10.0 g, 63.6 mmol) in DMF (25.0 mL) was charged with methyl iodide (5.94 mL, 95.5 mmol) and potassium carbonate (13.2 g, 95.5 mmol). The reaction mixture was stirred at rt for 16 h. The reaction was quenched with water (30 mL) and extracted with EtOAc (30 mL). The organic layer was washed with water (25 mL), washed with Brine (25 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to yield a brown oil, 11.0 g (101% yield). 1H NMR (CDCl3, 400 MHz): δ=4.08 (d, J=2.02 Hz, 3 H), 7.14 (td, J=8.34, 4.80 Hz, 1 H), 7.35 (ddd, J=10.74, 8.34, 1.64 Hz, 1 H), 7.58 (dt, J=8.27, 1.55 Hz, 1 H).

Provenance & Evidence